Mercury derivatives of substitution products of di-phenyl phenolphthalein



Patented Mar. 27, 1934 PATIENT oFFioE MERCURY DERIVATIVES" OF SUBSTITUTION PRODUCTS 0F DI-PHENYL P H E N 0 L PHTHALEIN Sidney E. Harris, Brooklyn, N. Y., and Walter G.-Cl 1rist ian sen, Bloomfield, N. .L, assignorsto E. R. Squibb & Sons; Brooklyn, N. Y.,- a corporation .of New York No Drawing. Application May 23,- 1931,

Serial No. 539,633

8 Claims. (01. 260-13) This invention relates to mercury derivatives of di-phenyl phenol phthalein and its substitution products.

In a co-pending application Ser. No. 539,632 filed May 23, 1931, we have described di-phenyl phenol phthalein and various derivatives there-.

of. These compounds have the general formula in which X is a monovalent substituent, especially hydrogen, a halogen, nitro, amino, or an alkyl.

The mercury derivatives are. believed to have the 'general structure I or II:

in which X is as in the general formula for di- Y may be hydroxyl, a halogen or other monov'alent radical. It is not certain that the mercury enters in exactly the position indicated by the formulae and it is not our intention to limit the invention to these exact compositions. Mercury derivatives of di-phenyl phenol phthalein and its substitution products are novel,', regardless of the position in which the mercury is found, and as such are a part of our invention.

The preparation of the products is illustrated in the following examples:

Example I.M0"no mercury compound of dibromo d'i phenyl phenol phthalein 6.3 glns. of dibromo diphenyl phenolphthalein are dissolved in 75 cos. of alcohol and heated to boiling. To the vigorously agitated boiling solution a solution of 3 gms. mercuric acetate in cos. water containing a small quantitysay 0.1 cos. of glacial acetic acid is added in a slow stream. The mixture is then boiled until inorganic mercury ions can no longer be detected in the liquid phase. The hot mixture is filtered and the precipitate washed thoroughly with alcohol and ether and finally dried in vacuo.

The product is a sandy amorphous powder, insoluble in water and the common organic solvents, but readily soluble'in dilute alkali solutions including ammonium hydroxide.

Example II.Di-mercury derivative of dinitro diphenyl phenol phthalein 3 gms. of dinitro diphenyl phenol phthalein are dissolved in cos. of alcohol and heated to boiling. To the well agitated boiling solution is added a solution of 6.8 gms. of mercuric acetate in 20 cos. of Water to which has been added a small quantity say 0.1 cos. of glacial acetic acid. The mixture is boiled with agitation till mercuric ions can no longer be detected in the liquid. The liquid is then allowed to cool and the precipitated dimercurated dinitro diphenyl phenol phthalein is filtered olT, washed with water, alcohol and ether and dried in vacuo. The product is a yellow p y phenol phthalein a its va v s and acetate and a small amount of glacial acetic acid.

2. The monoand di-mercury derivatives of a in an inert organic solvent are boiled with mercompcund represented by the formula: curic acetate and a small amount of glacial acetic acid.

a a 5. The compounds having substantially the 5 OH general formula:

OH Cells CoHs x CO 0 gY X in which X is a monovalent substituent, said derivatives containing mercury in the position it occupies when solutions of said compounds in CO inert organic solvents are boiled with mercuric acetate and a small amount of lacial acetic acid.

3. The monoand di-mercur y derivatives of a m Whlch X hydrogen halogen Intro ammo or compound represented by the formula: alkyl and Y 1s hydroxyl, a halogen or acetyl.

6. The compounds having substantially the general formula:

CuHs

HgY X GoHn CO 0 HEY X in which X is hydrogen, a halogen, nitro, amino, or an alkyl, said derivatives containing mercury 00 in the position it occupies when solutions of said compounds in inert organic solvents are boiled with mercuric acetate and a small amount of m Whlch X 15 hydrogen, halogen, Intro, ammo glacial acetic acid or alkyl and Y is hydroxyl, a halogen or acetyl. 4. The monoand di-mercury derivatives of 7. Mono mercury de v of d -p e yl the compound represented by the formula: 4,4 phenol phthalein, said derivatives containing 00H; mercury in the position it occupies when a solution in an inert organic solvent of the compound 03 from which the mercury derivative is formed is boiled with mercuric acetate and a small amount Br of glacial acetic acid.

8. Di-mercury derivatives of 3,3 di-phenyl 4,4 phenol phthalein, said derivatives containing 0 OH mercury in the position it occupies when a solu- 5 tion in an inert organic solvent of the compound from which the mercury derivative is formed is boiled with mercuric acetate and a small amount of glacial acetic acid.

00 said derivatives containing mercury in the posi- SIDNEY HARRIS- tion it occupies when solutions of said compounds WALTER CHRISTIANSEN- 

